US8083947B2 - Polymer-containing solvent purifying process - Google Patents
Polymer-containing solvent purifying process Download PDFInfo
- Publication number
- US8083947B2 US8083947B2 US12/391,344 US39134409A US8083947B2 US 8083947 B2 US8083947 B2 US 8083947B2 US 39134409 A US39134409 A US 39134409A US 8083947 B2 US8083947 B2 US 8083947B2
- Authority
- US
- United States
- Prior art keywords
- organic solvent
- polymer
- microfiltration
- developing solution
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 229920000642 polymer Polymers 0.000 title claims abstract description 28
- 239000002904 solvent Substances 0.000 title abstract description 11
- 238000001471 micro-filtration Methods 0.000 claims abstract description 23
- 238000007639 printing Methods 0.000 claims abstract description 16
- 239000011148 porous material Substances 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- -1 glycol dialkyl ethers Chemical class 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- 229920001400 block copolymer Polymers 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229910001220 stainless steel Inorganic materials 0.000 claims description 7
- 239000010935 stainless steel Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 235000007586 terpenes Nutrition 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 238000005189 flocculation Methods 0.000 claims description 3
- 230000016615 flocculation Effects 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 238000000108 ultra-filtration Methods 0.000 claims description 2
- 238000010923 batch production Methods 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 239000003791 organic solvent mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 10
- 238000004064 recycling Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- VJBCNMFKFZIXHC-UHFFFAOYSA-N azanium;2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)quinoline-3-carboxylate Chemical compound N.N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O VJBCNMFKFZIXHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 238000001029 thermal curing Methods 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000007647 flexography Methods 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/3092—Recovery of material; Waste processing
Definitions
- This invention relates to a method for purifying and optionally reusing (or recycling) polymer-containing solutions, such as those used in the production of flexographic printing plates. More specifically, this method relates to purifying such solutions using microfiltration as the primary purification means.
- Organic solutions are used in various industries for washing, developing, or cleaning various substrates or materials and as a result, the organic solutions generally become contaminated with various polymeric materials that are dissolved in the organic solvents of which the organic solutions are composed.
- washout or developing processes are known for the preparation of flexographic printing plates, and the developing solutions become contaminated with various polymeric and non-polymeric materials from the non-imaged portions of the flexographic printing plate precursors.
- Such developing processes are described for example in U.S. Pat. No. 5,240,815 (Telser et al.), U.S. Pat. No. 7,226,709 (Kidnie et al.), and U.S. Pat. No. 7,279,254 (Zwadlo) and in U.S. Patent Application Publication 2005/0227182 (Ali et al.).
- the flexographic printing plate precursors are imaged and then developed to remove non-polymerized material while leaving the polymerized (cured) material intact to form a relief image in the resulting flexographic printing plates.
- Various organic solvents are generally contained in such developing solution including but not limited to, chlorinated hydrocarbons, saturated cyclic or acyclic hydrocarbons, aromatic hydrocarbons, lower aliphatic ketones, and terpene hydrocarbons.
- flexographic printing plate precursors can be prepared from a variety of polymeric materials, it is usually necessary to match the imaged precursors with specific developing solutions so the non-polymerized materials can be quickly and completely removed to provide the relief images.
- Mechanical means such as brushing with rubbing means may be used to facilitate polymer removal.
- the present invention provides an improved method for purification, reclaiming, or recycling organic solvents from various industrial processes but particularly from the development of imaged flexographic printing plate precursors.
- this invention provides a method for purifying a polymer-containing solution consisting essentially of subjecting the polymer-containing solution to microfiltration using a tubular filter having an average pore diameter of less than 1 ⁇ m and a filtration pressure of at least 0.35 MPa to provide a purified solution.
- the present invention provides a method for purifying a polymer-containing flexographic developing solution comprising:
- a metal tubular filter having an average pore diameter of from about 0.02 to about 0.5 ⁇ m and a filtration pressure from about 1 to about 2 MPa and a flow rate of from about 15 to about 1,000 liters/min to provide a purified developing solution
- the developing solution containing one or more block copolymers of styrene and butadiene, block copolymers of styrene and isoprene, copolymers of butadiene and acrylonitrile, or copolymers of butadiene, acrylonitrile and acrylic acid.
- the method of this invention is an environmentally freed, simple, and inexpensive means for reclaiming or recycling organic solvents such as flexographic developing solvents. While known reclamation methods are suitable for removing particulates and relatively large materials, the present invention can be used to remove smaller materials because of the use of microfiltration tubes having average pore size below 1 ⁇ m. Distillation and other power consuming and expensive methods can be avoided. The reclaimed solvents can be reused if desired or discarded in an environmentally appropriate manner.
- FIG. 1 is a schematic diagram of one embodiment of this invention.
- the method can be carried out in a self-contained apparatus or by using separate equipment in different places. Most advantageously, the method is carried out in a self-contained manner so that the purified solvent can be readily recycled for reuse, for example, in a continuous manner.
- One system useful for this purpose is known as the Cold Reclamation System (CRS) that includes a continuous, tubular microfiltration process utilizing for example, stainless steel tubular filters.
- CRS Cold Reclamation System
- the method can also be carried out in a batch manner.
- Polymer-containing solution can be taken from “seasoned” holding tank 10 through microfiltration tubes 20 using one or more pumps (for example, pump 25 ) into purified solution holding tank 30 .
- the purified solution can be recycled, for example, to flexographic printing plate processing equipment 40 , thus making a fill cycle.
- Unused “fresh” solution can also be added from replenishment tank 50 .
- the various parts of the purification system illustrated in FIG. 1 can be obtained from various commercial sources.
- very useful microfiltration tubes generally have a pore diameter less than 1 ⁇ m, and more likely from about 0.02 to about 0.5 ⁇ m.
- Commercial examples of useful stainless steel tubular filter membranes are commercially available from Graver Technologies (Glasgow, Del.) as SCEPTER stainless steel tubular filter members.
- One such product is a TiO 2 -sintered membrane on a stainless steel support having an average pore diameter of about 0.1 ⁇ m.
- the polymer-containing solution can be pumped through the tubular filters at a pressure of at least 0.35 megapascals (MPa) (or 50 psi) and generally at from about 1 to about 2 MPa as a flow rate of from about 15 to about 1,000 liters/min (for example, about 15 to 50 liters/min going into the microfiltration tubes and up to 1,000 liters/min inside the microfiltration tubes).
- MPa megapascals
- the permeate is pushed through the microfilter tubular membranes for recirculation or storage for future use. Recycling allows for continuous processing, for example, of imaged flexographic printing plate precursors. Concentrate that may build up within the microfiltration tubes, and containing polymers and other undesired materials, can be disposed of in any suitable manner.
- the microfiltration process generally recirculates the polymer-containing solution as many times as needed to reduce the solid content to 3% or less and preferably to 1% or less.
- the method of this invention can be carried out at a temperature of from about 15 to about 50° C.
- the polymer-containing solution is a polymer-containing organic solution such as a flexographic printing plate developing solution.
- the solution may contains one or more block copolymers of styrene and butadiene, block copolymers of styrene and isoprene, copolymers of butadiene and acrylonitrile, and copolymers of butadiene, acrylonitrile, and acrylic acid.
- the polymer-containing solution generally contains one or more of the following organic compounds: dialkylene glycol dialkyl ethers, acetic acid esters, carboxylic acid esters, alcohols, terpenes, terpene esters, lower aliphatic ketones, aromatic hydrocarbons, saturated or alicyclic hydrocarbons, and chlorinated hydrocarbons, that can serve as solvents or solvent mixtures.
Abstract
Description
Claims (15)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/391,344 US8083947B2 (en) | 2009-02-24 | 2009-02-24 | Polymer-containing solvent purifying process |
PCT/US2010/000432 WO2010098819A1 (en) | 2009-02-24 | 2010-02-16 | Polymer-containing solvent purifying process |
EP10705020A EP2401061A1 (en) | 2009-02-24 | 2010-02-16 | Polymer-containing solvent purifying process |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/391,344 US8083947B2 (en) | 2009-02-24 | 2009-02-24 | Polymer-containing solvent purifying process |
Publications (2)
Publication Number | Publication Date |
---|---|
US20100213128A1 US20100213128A1 (en) | 2010-08-26 |
US8083947B2 true US8083947B2 (en) | 2011-12-27 |
Family
ID=42154477
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/391,344 Expired - Fee Related US8083947B2 (en) | 2009-02-24 | 2009-02-24 | Polymer-containing solvent purifying process |
Country Status (3)
Country | Link |
---|---|
US (1) | US8083947B2 (en) |
EP (1) | EP2401061A1 (en) |
WO (1) | WO2010098819A1 (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8083947B2 (en) * | 2009-02-24 | 2011-12-27 | Eastman Kodak Company | Polymer-containing solvent purifying process |
US8349185B2 (en) | 2010-10-20 | 2013-01-08 | E I Du Pont De Nemours And Company | Method for rebalancing a multicomponent solvent solution |
US8530142B2 (en) | 2011-03-15 | 2013-09-10 | Eastman Kodak Company | Flexographic printing plate precursor, imaging assembly, and use |
CN103631099A (en) * | 2012-08-22 | 2014-03-12 | 财团法人印刷工业技术研究中心 | Environmental-friendly plate processor applied to water washing type printing plate materials |
US9309205B2 (en) | 2013-10-28 | 2016-04-12 | Wincom, Inc. | Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures |
CN106547176A (en) * | 2015-09-21 | 2017-03-29 | 乐凯华光印刷科技有限公司 | A kind of developer solution suitable for the photosensitive CTP plates of low chemical treatment |
RU2622404C1 (en) * | 2016-01-19 | 2017-06-15 | Публичное акционерное общество "СИБУР Холдинг" | Method for clearing liquid hydrocarbons of high molecular impurities |
CN107986569B (en) * | 2017-12-14 | 2021-04-02 | 东华大学 | High-nitrogen printing wastewater treatment and recycling system and use method thereof |
JP2019179091A (en) * | 2018-03-30 | 2019-10-17 | 住友理工株式会社 | Developing method of printing plate and developing device |
CN111995187A (en) * | 2020-08-25 | 2020-11-27 | 上海吾励环境技术有限公司 | Acrylonitrile wastewater treatment method |
WO2024048625A1 (en) * | 2022-09-02 | 2024-03-07 | 旭化成株式会社 | Method and device for treating aqueous developer waste liquid, and development system |
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US4776999A (en) * | 1986-10-10 | 1988-10-11 | Hoechst Celanese Corporation | Ultrathin polyether sulfone polymer films and their preparation |
EP0430233A2 (en) | 1989-11-30 | 1991-06-05 | Toyo Boseki Kabushiki Kaisha | Process and apparatus for developing photopolymer plates |
US5041227A (en) | 1990-10-09 | 1991-08-20 | Bend Research, Inc. | Selective aqueous extraction of organics coupled with trapping by membrane separation |
US5240815A (en) | 1990-06-27 | 1993-08-31 | Basf Aktiengesellschaft | Production of photopolymeric flexographic relief printing plates |
US5322761A (en) * | 1992-06-04 | 1994-06-21 | Minnesota Mining And Manufacturing Company | Flexographic printing plate having a vanadium oxide antistatic coating layer |
US5354645A (en) | 1988-08-23 | 1994-10-11 | E. I. Du Pont De Nemours And Company | Process for the production of flexographic printing reliefs |
WO1997003382A1 (en) | 1995-07-13 | 1997-01-30 | Polyfibron Technologies, Inc. | Making a photopolymer printing plate |
US5605633A (en) * | 1993-11-29 | 1997-02-25 | Fuji Photo Film Co., Ltd. | Process for treating photographic waste water |
US5734944A (en) * | 1994-08-24 | 1998-03-31 | Bayer Corporation | Apparatus for rejuvenating developer in printing plate development |
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US6180009B1 (en) | 1996-01-12 | 2001-01-30 | Vantico Inc. | Method of filtering the organic solutions arising in the production of circuit boards |
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US6897008B1 (en) | 2003-11-06 | 2005-05-24 | Nupro Technologies, Inc. | Terpene ether developing solvent for photopolymerizable printing plates |
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2009
- 2009-02-24 US US12/391,344 patent/US8083947B2/en not_active Expired - Fee Related
-
2010
- 2010-02-16 EP EP10705020A patent/EP2401061A1/en not_active Withdrawn
- 2010-02-16 WO PCT/US2010/000432 patent/WO2010098819A1/en active Application Filing
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Also Published As
Publication number | Publication date |
---|---|
WO2010098819A1 (en) | 2010-09-02 |
EP2401061A1 (en) | 2012-01-04 |
US20100213128A1 (en) | 2010-08-26 |
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